A Night to Remember
by NFlippers
Summary: Sam has loved Dean forever, is it the right time to take the risk? Wincest. Sam/Dean. Rated M for mature content and some coarse language. Reviews are greatly appreciated.


A Night To Remember

Sam had always loved Dean, more than a brother. He had always wanted to be with him for as long as he could remember, to him, it was just normal. Every time Sam looked at Dean it drove him wild, knowing that he couldn't possibly have his own brother, right? It was one of those things, so tempting, yet not possible. Whenever he hinted at the fact, Dean constantly shot him down, cutting him off, giving him an awkward glare; he was just waiting for the right moment when he could show his true self to his brother.

So the story begins, in one of those cheap motels on the highway, in the middle of nowhere. They had stopped for the night after coming off a case dealing with the reapers, some mass death in a small town. They had been driving for a few hours after they had solved the case and it was getting late, they were both pretty worn out and decided to check in for the night; tomorrow they would get an early start towards their next case, or so they thought.

Tonight they picked a room at random and it turned out to have only one massive king size bed that took up most of the floor space in the room. They hauled their things inside and Dean went to take a quick shower before tucking in for the night. Sam was having a really hard time controlling certain…feelings today and thought that tonight might be the perfect chance, the perfect setting to risk it all. He wasn't usually a big risk-taker but something urged him on, whether it was his lust for his brother or just his sleep-deprived brain going wild on him, he knew tonight could be the night; the night that he finally makes it with his big brother.

Sam quickly unclothed and hopped into the bed, waiting for Dean to be finished his shower, little did he know his baby brother was waiting for him in the bed they were to share, completely naked. Sam heard the water stop hissing and knew it would be a matter of minutes before his brother emerged from the bathroom. He was getting aroused just by thinking about his brother, all wet after his shower, only a towel separating him from complete and utter nudity. Sam began to imagine his brother and what they might do tonight, he was so deep in thought that he hadn't heard Dean come out of the bathroom and walk towards the bed.

"Sammy, you having a shower?" he asked, almost certain the answer would be no, since Sam usually always showered in the morning.

"Uhh, no. No I'm not having one now, I'll have a shower in the morning," Sam replied quickly, snapping himself out of his daydreaming.

"Knew it," Dean smirked.

"Well then, why'd you ask?" answered Sam in a smart-ass tone.

"Just thought you might change your mind tonight, I know everything about you anyways," Dean smiled crookedly and sat on the bed, back facing his little brother.

Sam stared at his brother, who was just sitting there on the edge of the bed, with only a towel wrapped loosely around his waist. He stared at the contours of his older brother's back and was mesmerized by the way a few stray drops of water trickled down his back. He was grateful that the covers were hiding his huge erection from his brother and hoped to keep it out of sight until the right moment.

"You only think you know everything about me…" Sam commented, trailing away as if his words caught in his throat.

"Oh, is that right?" Dean asked, genuinely interested. When Sam didn't reply he slipped off the towel and slipped under the covers.

"Y-your sleeping naked tonight?" Sam asked, kind of stuttering, although he didn't want Dean to think that he was uncomfortable with it.

"Yeah, got a problem with it Sammy? It's been a long day and it's nice to just relax and let loose once in a while." Dean replied.

Sam found it interesting that his brother would pick tonight of all nights to sleep naked, since they were sharing a bed this time. He had no problem with it and thought it would make it easier to make his move tonight. He made sure that Dean couldn't tell that he too was naked under the covers, shifting over a bit to give his brother some more room.

"Nope, no problem," Sam answered, a little more quickly than he had hoped. He gulped and summoned up his courage to move towards Dean who again had his back turned to Sam.

Sam inched his way over to his brother's side of the bed, making sure that his erection didn't reach Dean before his lips did. He stretched out his arms and wrapped them around his brother and kissed the back of Dean's neck.

Dean practically leapt out of the bed and stood before Sam completely naked. "What the hell dude?" Dean asked, not knowing what was going through his little brother's mind.

"Dean, come on, just get back in the bed," Sam replied in a hurry. He flipped the covers off to reveal to Dean that he was also naked.

Dean was staring at his little brother, thoughts spinning through his mind. _Is he really naked or am I just seeing things? _He thought to himself, _Wow, Sammy sure is packing a big one._ Bad thoughts started playing in his mind, thoughts about him slamming a kiss onto his younger brothers' lips. This was wrong, right? It had to be wrong. Dean hadn't hooked up with anyone for a while, but, he couldn't be having these thoughts about his brother, not about Sammy! As his brother lied there completely naked in front of him, he noticed that he started to get hard.

"Looks like you are just as happy as I am that his is happening," Sam smirked and hopped out of bed.

Dean was just standing there, exposed, so Sam walked up to him slowly and kissed him straight on the lips. That got Dean in the mood; he was completely hard now, ready to go.

"Does this mean I'm gay?" Dean asked, it seemed to be a stupid question. Of course he was, now that he thought about it, he was only hooking up with as many girls as he could to make his brother jealous. He didn't wait for an answer but began kissing his brother back. He was willing to give everything up for his brother, even his sexuality. Dean pulled away from his brother only to ask him one question, "So, all those glances and touches from you; you've been giving me signals that you wanted this to happen haven't you?"

"Of course, I wanted you bad ever since I could remember, looking at you shirtless gave me my first hard-on, I mean, thinking of you is what gets me off every night," Sam replied. "Now lets get back over to the bed and see what happens, I'm sure it'll be great."

They both walked back over to the bed and climbed in. They began kissing each other, holding each other closely, as if they would never let go.

"Let's do it then, now, hard," Dean panted as they came apart from an unusually long kiss.

"I'd love to!" exclaimed Sam, wanting his brother inside him so badly right now he could burst.

Dean leaned over and gave Sam a few kisses before reached for his duffel bag that was laying on the floor beside the massive bed. He grabbed some lube and squeezed some out over his fingers. "You sure you want to do this?" he asked.

"Are you kidding, I've wanted to do this since I knew what sex was!" Sam replied, getting ready for the best night of his life.

"Okay..." That was all Dean needed to hear and he plunged two fingers into his brother's ass.

Sam gasped, loving the sensation of his brother fingering him.

"Wow, you have a pretty tight ass Sammy," Dean commented giving his little brother a quick wink.

"Well it's not like I get some stranger to fuck me every day, this will be my first time getting fucked and I was saving it for you. Now shut up and just keep going." Sam smiled and tilted his head back into the pillows as he felt his brother's fingers moving inside of him.

Dean pulled out his fingers and noticed that Sam had pre-cum dripping down the side of his dick, he licked it up and it made Sam go crazy. Dean shifted around so he was straddling his brother and he grabbed Sam's long brown hair and motioned his brother's face towards his dick. It didn't take Sam too long to catch on and within seconds Dean was moaning as his little brother took it all in his mouth, he gave one great blowjob.

Dean pulled out of Sam's mouth and went back to the lube. He squirted some onto his hard-on and rubbed it down good. He put Sam's legs on his shoulders and lined his dick up with his little brother's ass. He went for it and shoved it in slowly, making Sam moan very loudly. _"Dean!"_ he moaned. He knew he just had to keep this up until he was about to cum. He kept up a good pace going in and out quite rhythmically. Sam moved his hips around wildly so he got the full force of having his brother fuck him good for the first time.

Without even having touched his own dick Sam yelled out his brother's name as his stomach muscles churned and a fountain of cum formed a pool on his stomach. He laid there gasping for breath as his brother just kept going, in and out. He got up on his elbows high enough to get a kiss from Dean, a kiss so passionate Sam thought he was going to melt.

Dean's breathing now seemed to be coming in spurts and he knew it wouldn't be long before he would cum. Sam's ass was constricting around Dean's dick after he had come and he knew it wasn't long before he would spill his own load. He stopped fucking Sam and pulled out. Sam was still breathing heavily and he was staring into Dean's emerald eyes, loving the look of satisfaction that Dean was giving him back.

"You aren't going to cum inside of me?" Sam inquired, sort of brought down.

"Not tonight Sammy, no, tonight I'm going to shoot my load all over your face." Dean replied.

"Oh yeah, come on Dean, do it! Cum all over my face." Sam encouraged his brother on.

Dean once again began straddling his baby brother who by now had gone soft and was trying to catch his breath. He sat there on top of his little brother stroking evenly until his whole body started quivering. Sam sat up and held his brother at the hips and licked the tip of Dean's dick.

"Yeah, come on Dean, do it," said Sam, sticking two fingers into Dean's ass, knowing he would cum as soon as he did it.

This sent Dean over the edge; his body quivered and he let out a huge sigh, and moaned for at least a minute before he finally stopped shooting his hot, white cum all over his little brother's face. They shared a kiss before Dean broke the silence.

"How was that Sammy, all you ever wanted?" he asked.

"All I could ever wish for and more, I hope we can do this all the time now, not only are you my brother, but you are also my lover. I like it that way." replied Sammy.

"Looks like I'm going to have to have another shower and get washed up, you want to join me this time Sammy?" asked Dean, laughing a bit and shining his beautiful million-dollar smile.

"Definitely wouldn't want to miss out on it…" Sam sighed and they both got up and headed for the bathroom.

It had been the most perfect moment in Sam's life when Dean kissed him back and now they could be together, not just as family, as something much, much more.


End file.
